In recent years, some of commercially available insecticides are restricted in their use in view of problems of persistency, accumulation and environmental pollution. Further, by using the same type of insecticides for a long period of time, generation of resistant pest insects is growing to be a problem. Therefore, it has been desired to develop an insecticide having a novel structure, which is considered to have a mode of action different from that of the commercially available insecticides.
Heretofore, as the N-heteroaryl-4-(trifluoromethyl)nicotinamide derivative, for example, Japanese Provisional Patent Publication No. Hei 10-195072 describes compounds having a 2-thiazolyl group or a 1,3,4-thiadiazole group as a heteroaryl group, and noxious animal controllers containing those as an active component. However, these compounds are different in the heteroaryl group from those of the invention in this application, and moreover, are insufficient in an insecticidal effect thereof.
Furthermore, a 4-trifluoromethylpyridine having a cyano group, a carbamoyl group or a carboxyl group at position 3 is useful as a manufacturing material of pesticides or medicines, and can be a intermediate of the N-heteroaryl-4-(trifluoromethyl)nicotinamide derivative.
As a production method of this intermediate, conventionally known are Journal of Medicinal Chemistry, vol. 10, 1967, pp. 149–154, Japanese Provisional Patent Publication No. Hei 6-321903, Japanese Provisional Patent Publication No. Hei 7-10841 and Japanese Provisional Patent Publication No. 2000-38385, etc. Among these, Journal of Medicinal Chemistry, vol. 10, 1967, pp. 149–154 describes that 3-cyano-4-trifluoromethylpyridine is an intermediate for the production of a lipolysis inhibitor produced by converting a cyano group into a tetrazolyl group. Further, Japanese Provisional Patent Publication No. Hei 6-321903, Japanese Provisional Patent Publication No. Hei 7-10841 and Japanese Provisional Patent Publication No. 2000-38385 describe that 4-trifluoromethylpyridine having a cyano group or a carbamoyl group at position 3 is an intermediate for the production of a noxious animal controller.
However, the above-described methods have a problem that the number of steps is large or a step having rigorous reaction conditions is contained; therefore, it has been desired to develop a more industrially advantageous production method.